All Bets Are On
by sai-salamander
Summary: Jake loses a bet with Sherry and now has to follow through with the consequences. Sequel to On Bets and Their Consequences. Crossdressing, Jake/Sherry


**A/N:** it has taken me a LONG time to finish this for some reason. Anyway, this is the sequel to Of Bets and Their Consequences, so it might not make much sense without reading that? Either way, crossdressing, f/m, pretty much pwp.

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The journey back to Sherry's place seemed to pass as slow as waiting for a siege to end. The blocks flashed by and Jake drummed on the wheel as he drove, both trying and failing to not steal glances at Sherry. Or, to be more precise, the steel blue dress she was wearing.

He cleared his throat and riveted his eyes firmly to the road, whistling under his breath to try and distract himself, which worked for all of ten minutes and then they were outside Sherry's apartment block.

Jake parked and they mounted the stairs in mutual silence, expectation lingering between them with an undertone of unspoken desire sparking like electricity whenever they brushed against each other. He followed Sherry up the stairs as ever, hands stuffed in his pockets and trying to act nonchalant.

"I can tell you're trying to act cool," Sherry said over her shoulder. "Can't fool me, Mr Muller."

"What, you get psychic powers along with that healing, super girl?"

"I don't need psychic powers to read you. You're like an open book sometimes, you know." Sherry unlocked the door and ushered him in, her hand on the small of his back, before locking it behind them again. They both kicked off their shoes.

The corridor was dim after the brightness of the day outside. It took Jake's eyes a little time to adjust, so he was caught completely off-guard when Sherry got all up in his business and pushed him against the wall, one hand firm on his shoulder. "You're not going to chicken out of this one, are you?"

Jake looked her directly in the eye, a smirk pulling at his mouth. "Hell no," he said, reaching down to pull Sherry closer, his hands on her waist. "You gotta take this off first though."

Sherry picked his hands off her with a smile of her own. That pseudo-innocent one that was Jake's complete favourite. "And wouldn't you just love that?" she asked, looking up at him and bunching her fists in his shirt. She took a step backwards, pulling him with her, then walked him the few paces to her bedroom, shoving him down onto the bed.

He leaned backwards on one arm, the other hand in his lap, and watched Sherry from under lidded eyes as she reached down for the hem of her dress. She pulled it up and over her head in one sweet movement, exposing navy lace-topped panties and a complete lack of bra. Draping the dress across her bed she set to work on the buttons on his shirt, which came apart willingly at her deft fingers.

With a little smile, Sherry peeled it off, exposing his skin to the air. The tautness of his muscles and the way they shifted as he moved never failed to stir her, and that moment was no exception. Suddenly hungry for touch, Sherry pulled Jake up off the bed and pressed herself to him, fumbling with his jeans as his hands went to her ass, pulling her in tighter and digging his fingertips in hard enough to elicit a gasp. "Oh no," she said, unzipping his jeans and pushing them down. "You're not distracting me that way." She leaned around him for the dress.

"Babe," Jake said with a grin, "I always pay my debts."

"Even if they're just bets?" Sherry held the dress up against his chest. "The colour suits you."

Jake put his hand over hers. "Especially if they're just bets. Don't wanna ruin my rep, do I?"

"Yeah, no one would have you if word got round. Arms up."

Jake ran his hands up Sherry's body, pausing only to graze her nipples with his thumbs and then straight on past and up above his head. His boxers, faded black, showed the evidence of his interest plainly. "Don't have all night, babe."

It took standing on her tiptoes, but Sherry managed to slip the dress over his arms. She tugged it down, noting the way it clung to his chest, a lot tighter on his larger frame than on hers. It wasn't even a particularly fancy dress - just a simple, plain blue tunic with no sleeves and a straight neckline that showed off his collarbone.

He shuffled a little, pulling the dress as far down as it would go, which was just enough to cover his boxers. "So whatcha think?" he asked, raising a sardonic eyebrow. "Looks better on me, huh?"

Sherry smiled at him, the little quirk at the corner of her mouth the best indication of her thoughts as usual. "I think you might look better out of it," she said, her glance flickering up and down the lines of his body. The dress seemed to accentuate his best features - that taut stomach, the way his hips jutted in that way she found so attractive. "Doesn't do anything for your legs though."

Jake swatted her on the arm then pulled her in close for a deep kiss, his hands in the small of her back. "I don't see ya complainin'," he said into her mouth.

"The only thing I'm complaining about is how you make that dress look hotter than I do."

"And what ya gonna do about that, super girl?"

Sherry hummed under her breath, head tilted to one side as if contemplating her answer. She grinned up at Jake, lust clear in her eyes. "Oh, I'm sure we can think of something." Setting her hands against his chest, she shoved him down onto the bed and crawled after him.

Jake's hands moved down to remove his boxers, but Sherry clucked her tongue and moved them away, pinning his wrists with her left and slipping the boxers down with her right. Jake squirmed to help, lifting his ass and then hissing as Sherry freed his erection only for it to be covered up again by the hem of her dress.

"Enough with the teasing, super girl." His voice was harsh and impatient, but Sherry just chuckled, looking up at him through her eyelashes.

"Or what? You can't negotiate in a bet, you know."

Jake mock-glared at her. "This wasn't in the terms and-" his words were cut off by a moan as Sherry traced the length of his cock through the fabric. He bucked his hips, and Sherry obliged, lifting the fabric up and off and replacing fingers with tongue. She took the head into her mouth, pressing her tongue to the underside and sliding him further inside. He jerked upwards, one hand finding her hair and the other grabbing a handful of blanket.

"Fuck," Jake gasped as Sherry dug her fingernails into his hips and stomach, keeping him pinned to the bed as she took him deeper. She had no desire to choke, even though her gag reflex was actually pretty impressive.

Jake's fingers caught a handful of her hair and he tugged her head up and off, inhaling as she let go of his cock.

"Impatient," Sherry said, brushing the corner of her mouth with the pad of her thumb. "It's usually the other way round."

"Guess I like this more than I thought," Jake said with a growl. "Get up here and kiss me, super girl."

"Oh, just a kiss now? I thought you were complaining about me being a tease a minute ago." Sherry nipped at his forearm, his fingers still in her hair. She moved herself further up his torso, planting her knees to either side of his hips and stretching out to kiss his bottom lip. Jake's hands moved in response, running the length of Sherry's body to grab her ass and pull her in closer.

"Didn't say kiss only," he said between breaths. "You gonna fuck me or do I have to beg?"

Sherry circled her hips, the pressure against her clit making her gasp and grind down harder. She slipped a hand between them, moved her hips and slipped Jake inside just a fraction, exercising all her control to just keep him there. He looked right into her eyes and pushed upwards, just as fractionally, that look in his eye that always spelled competition.

A groan, but from both their lips, as they gave in to the pressure and moved. Jake sunk as deep as he could go into Sherry, his hands on her ass and pulling her tighter to him. She gasped into his mouth as his pelvis pressed against her clit.

"Shit, Jake," she breathed, slamming one hand down on the bed at the side of his head. He smirked, rolling his hips in response.

"Yeah, you like that baby?" He began a smooth rocking motion, hips moving continuously and oh so slowly until he began to feel heat coil within him.

Sherry brought her arms up and encircled Jake's head, leaning down to kiss him deep and long as they breathed and rocked together. Her dress slid between them, the movement oddly sensual.

Jake's hands at her ass pulled Sherry down onto him as deeply as she could fit, and the movement of his hips drove his dick into her at just the right angle. Coupled with the pressure and friction against her clit, it was enough to send Sherry gasping into her orgasm, forehead pressed against Jake's cheek and eyes squeezed shut as her whole body clenched around him.

She was dimly aware of Jake jerking in response, coming swiftly after her as she shivered with aftershocks. His arms were tight around her as she sagged on top of him, boneless and loose and still gasping. "That was intense," he murmured into her ear, chasing the words with a kiss to the temple. "God, I fucking love you."


End file.
